Methane → Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 247490Notes

Reaction equation

HRID 247490 reaction equation
[F:1][C:2]([F:30])([F:29])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[C:9]2[C:13]([O:15]CC1C=CC=CC=1)=[O:14])[OH:4].C.C(=O)(O)[O-].[Na+:36].O1CCOCC1>[Pd].O>[F:30][C:2]([F:1])([F:29])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[C:9]2[C:13]([O-:15])=[O:14])[OH:4].[Na+:36]

Participants

7

Reactant 4

HCID 297MethaneHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 20160992Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 23674972Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (25 mg), 10% palladium on powdered charcoal (25 mg), sodium bicarbonate (5 mg), dioxane (2 ml), and water (1 ml) is hydrogenated at 40 psi for 30 mins. The mixture is filtered to remove the catalyst which is washed with water (3×2 ml). The combined filtrate is extracted with ethyl acetate (2×2 ml), concentrated in vacuo, and lyophilized to give sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with water (3×2 ml)
  4. extractionThe combined filtrate is extracted with ethyl acetate (2×2 ml)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2aac9ae023e44af898fd1d2e293e4f1b
Source dataset
uspto-grants-1987_11
Patent number
US04707547

Reaction notes

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